Enantioselective Allylic Amination of Morita-Baylis-Hillman Carbonates Catalysed by Modified Cinchona Alkaloids

An efficient procedure for the asymmetric allylic amination of Morita–Baylis–Hillman carbonates with cyclic imides catalysed by commercially available cinchona alkaloids is reported. It proves to be a facile protocol that affords α‐methylene β‐amino esters with good‐to‐excellent enantioselectivities...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2009-11, Vol.2009 (33), p.5804-5809
Main Authors: Zhang, Shan-Jun, Cui, Hai-Lei, Jiang, Kun, Li, Rui, Ding, Zhen-Yu, Chen, Ying-Chun
Format: Article
Language:English
Subjects:
Alkaloids
Amination
Asymmetric catalysis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Organocatalysis
Preparations and properties
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Summary:An efficient procedure for the asymmetric allylic amination of Morita–Baylis–Hillman carbonates with cyclic imides catalysed by commercially available cinchona alkaloids is reported. It proves to be a facile protocol that affords α‐methylene β‐amino esters with good‐to‐excellent enantioselectivities (up to 94 % ee) and in high yields (up to 97 %). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) The asymmetric allylic amination ofMorita–Baylis–Hillman carbonates with cyclic imides catalysed by a modified cinchona alkaloid (DHQD)2PYR has been developed. An array of α‐methylene β‐amino esters were obtained with good‐to‐excellent enantioselectivities (up to 94 % ee) and in high yields (up to 97 %).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200900944